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We report here the difference between phenyl propanoid glycosides obtained from hot water and methanol extracts of lemon peel. Eight phenyl propanoid glycosides were isolated, and their structures were established by UV, MS, 1H-NMR and 13C-NMR spectroscopy, as well as by chemical evidence. They were coniferin (1), syringin (2), dehydrodiconiferyl alcohol-4-β-glucoside (3), citrusin A (4), citrusin B (5), citrusin C (6), methyl-3-(4-β-glucopyranosyl-3-methoxyphenyl)propionate (7) and methyl-3-{4-(6-O-α-glucopyranosyl-β-glucopyranosyl)-3-hydroxyphenyl}propionate (8). Compound 7, after intravenously injecting (0.5 mg/100 g of body weight) into stroke-prone spontaneously hypotensive rats (SHR-SP), was found to lower the blood pressure. Among these isolated compounds, 7 and 8 are new phenyl propanoid glycosides.

Four cyclic peptides were isolated from young unshiu (unripe fruit), orange and amanatsu peelings, and their structures were established on the basis of FAB-MS (CID method) and 2D-NMR spectroscopic data, and by chemical evidence. They were each found to consist of seven or eight amino acids.

Mutants of Dictyostelium discoideum were isolated and found to be defective in the epitope recognized by the monoclonal antibody 120 against the carbohydrate moieties of an integral membrane glycoprotein, contact site A, with the apparent molecular mass of 80 x 10(3). One mutant, HG764, did not express any contact site A and had lost cell contact resistant to EDTA. The others, including HG794, expressed a 68-kDa form of contact site A. In comparison with the parental strain HG592, HG794 showed weaker EDTA-resistant cell contact and the same degree of EDTA-sensitive cell contact. This suggested that the moieties which HG794 lacked were involved in EDTA-resistant cell contact. The 68-kDa contact site A in HG794 could be labeled with wheat germ agglutinin and incorporated [35S] sulfate. The modB mutant HL220 also expresses 68-kDa contact site A, although it cannot be labeled with wheat germ agglutinin. Therefore, the mutants HG794 and HL220 were compared by a complementation test. The diploid strain DG701 expressed 80-kDa contact site A and showed the same degree of EDTA-resistant cell contact as strain HG592. In its EDTA-resistant cell contact, HG794 was stronger than HL220. These results suggest that HG794 is a new mutant, and that there might be at least two processes in the glycosylation of 68-kDa contact site A to the 80-kDa form. The carbohydrate moieties recognized by monoclonal antibody 120 and by wheat germ agglutinin might be involved in EDTA-resistant cell contact.

We report here the difference between phenyl propanoid glycosides obtained from hot water and methanol extracts of lemon peel. Eight phenyl propanoid glycosides were isolated, and their structures were established by UV, MS, 1H-NMR and 13C-NMR spectroscopy, as well as by chemical evidence. They were coniferin (1), syringin (2), dehydrodiconiferyl alcohol-4-β-glucoside (3), citrusin A (4), citrusin B (5), citrusin C (6), methyl-3-(4-β-glucopyranosyl-3-methoxyphenyl)propionate (7) and methyl-3-{4-(6-O-α-glucopyranosyl-β-glucopyranosyl)-3-hydroxyphenyl}propionate(8). Compound 7, after intravenously injecting (0.5 mg/100 g of body weight) into stroke-prone spontaneously hypotensive rats (SHR-SP), was found to lower the blood pressure. Among these isolated compounds, 7 and 8 are new phenyl propanoid glycosides.

Two limonoid glycosides were isolated from lemon peel, and their structures were established on the basis of FAB-MS data, 2D-NMR spectroscopic data, and chemical evidence to be ichangin 4-β-glucopyranoside (1) and nomilinic acid 4-β-glucopyranoside (2).In the present study, compounds 1 and 2 are shown to be new limonoid glycosides.

Two limonoid glycosides were isolated from lemon peel, and their structures were established on the basis of FAB-MS data, 2D-NMR spectroscopic data, and chemical evidence to be ichangin 4-β Jglucopyranoside (1) and nomilinic acid 4-β-glucopyranoside (2). In the present study, compounds 1 and 2 are shown to be new limonoid glycosides.

Two coumarin derivatives were isolated from hassaku (Citrus hassaku HORT.), zabon (Citrus gradis OSBECK.) and amanatsu (Citrus natsudaidai) peeling. Their structures were determined by means of MS, 1H-NMR and 13C-NMR spectroscopy.8- (2, 3-dihydroxy-3-methylbutyl) -7-methoxycoumarin (1) and 7- [(6, 7-dihydroxy-3, 7-dimethy1-2 E-octenyl) oxy] coumarin (2) were found.Compound (1) was intravenously injected into SHR-SP rats (1 mg/100 g body weight) with subsequent rise in blood pressure. Compound (2) was not tested owing to its poor solubility in water.

(1990). Structure and Physiological Activity of Phenyl Propanoid Glycosides in the Leaf of Hinoki (Chamaecyparies obtusa SIEB, et ZUCC.) Agricultural and Biological Chemistry: Vol. 54, No. 2, pp. 557-559.

Organisms have catalase, l-ascorbate peroxidase (AsAPOD), and glutathione peroxidase (GSHPOD) capable of scavenging H2O2, one of the toxic forms of O2. Catalase with a low affinity for H2O2 is found only in peroxisomes and cannot decompose the lipid hydroperoxides. Thus, AsA- and GSHPODs detoxify such active oxygens in energy-generating organelles. While both peroxidases have the same function in protection of the cell from oxidative damage, the distribution of the peroxidases is apparently distinct: AsAPOD occurs only in plant tissues, protozooa, and algae, while GSHPOD is only present in animal tissues (1).

An attempt was made to isolate hypotensive substances from a hot water extract of yuzu. Eight flavonoid glycosides were isolated by repeated chromatography and gel filtration after extraction with butanol and treatment with lead subacetate. Their structures were established by UV, MS, 1H-NMR and 13C-NMR spectroscopy, and sugar analysis to be 3, 8-di-C-glucosylapigenin (1), hesperidin (2), naringin (3), narirutin (4), homoeriodictiol 7-[2-O-α-rhamnosyl-β-glucose] (5), hesperetin 7-{[α-rhamnosyl(1→2)]-[α-rhamnosyl (1→6)]-β-glucose} (6), naringenin 7-{[α-rhamnosyl (1→2)]-[α-rhamnosyl (1→6)]-β-glucose} (7) and (-)-cis-3, 5, 7-trihydroxy-3'-methoxyflavanone 7-[2-O-α-rhamnosyl-β-glucose] (8). Among these compounds, 7 and 8 were a new flavanone and dihydroflavonol glycoside, respectively. Each component was intravenously injected into SHR-SP rats (1.0mg/100g body weight), and a hypotensive effect was weakly present in only 7.

ワックス・エステルのラット生育や各臓器に及ぼす影響を検討するために, ワックス・エステルを多量に含むEnglenaの給餌と, ワックス・エステルの強制経口投与を行なった。給餌実験では, Eecglena食群はカゼ身ソ食群と同様の生育を示し, 両群で有意な差は認められなかった。また両群の相対臓器重量も, ほとんど変化がなかった。糞量は, Euglena食群で有意な増加が認められたが, これはEuglenara含まれる非消化性の貯臓多糖であるパラミロソ (β-1, 3-グルカン) によるものであった。Euglena食群の尿量は, カゼイン食群に比べて有意に滅少していた。糞中へのワックス・エステル排泄量は, 投与量のわずか1.5%であり, 各臓器・組織中にも著しい蓄積は認められなかった。 精製ワックス・エステルを強制的に経口投与しても, 生育と食餌摂取量は, 無投与群とまったく変わらなかった。また, 糞・尿排泄量や相対臓器重量にもまったく影響を及ぼさなかった。糞中のワックス・エステル量は, 投与量の2.8%にすぎず, 各臓器や血液にも, ほとんど検出されなかった。 以上より, 投与したEuglenaワックス・エステルは, ラット生育に影響を及ぼすことなく, 活発に代謝・吸収されていることがわかった。

Optically pure (R)- and (S)-3-hydroxybutanoic acid and its homologues are prepared by the method consisting of the enantioface differentiating hydrogenation of methyl 3-oxoalkanoate to methyl 3-hydroxyalkanoate(80–90% e.e.) over asymmetrically modified nickel catalyst and the preferential crystallization of optically pure 3-hydroxyalkanoic acids from the hydrogenation products as the dibenzylammonium salts.

An attempt was made to isolate the hypotensive substances from a hot water extract of kinkan. Eight flavonoid glycosides were isolated by repeated chromatography and by gel filtration after extracting with n-butanol and treating with lead subacetate. Their structures were established to be 6,8-di-C-glucosylapigenin (1), 3,6-di-C-glucosylacacetin (2), 2″-O-α-l-rhamnosyl-4′-O-methyl-vitexin (3), 2″-O-α-l-rhamnosyl-4′-O-methylisovitexin (4), 2″-O-α-l-rhamnosylvitexin (5), 2″-O-α-l-rhamnosylorientin (6), 2″-O-α-l-rhamnosyl-4′-O-methylorientin (7) and ponicilin (8) by UV. MS, 1-NMR and 13C-NMR spectroscopy, and by sugar analysis. Each component was intravenously injected in SHR-SP (0.5 ~ 1.0 mg/100 g of body weight), 1, 2, 5 and 6 were found to lower the rat blood pressure.Among these compounds, 2, 3, 4, 6 and 7 were new flavone glycosides.

An attempt was made to isolate hypotensive substances from hot water extracts of lemon peels. Eight flavonoid glycosides were isolated by repeated chromatography after extraction with butanol and treated with lead subacetate. Their structures were established by UV, MS, 1H-NMR and 13C-NMR spectroscopy, and sugar analysis to be : 6, 8-di-C-glucosyldiosmetin (8), 6-C-glucosyldiosmetin (9), 8-C-glucosyldiosmetin (10), isovitexine (11), apigenin 7-[6-O-α-rhamnosyl-β-glucose] (12), limocitrin 3-0-{[3-hydroxy-3-methylglutarate(1→2)]-β-glucose} (13), limocitrin 3-0-{[5-α-glucosyl-3-hydroxy-3-methylglutarate(1→2)]-β-glucose} (14) and limocitrol 3-O-{[5-α-glucosyl-3-hydroxy-3-methylglutarate(1→2)]-β-glucose} (15). Each component was intravenously injected into SHR-SP rats (1.0mg/100g body weight), and 8 was found to lower blood pressure. Among these compounds, 13, 14 and 15 were new flavonol glycosides.

An attempt was made to isolate hypotensive substances from a hot water extract of Citrus unshiu. Six flavonoid glycosides were isolated by repeated chromatography and gel filtration after extraction with butanol and treatment with lead subacetate. Their structures were established to be limocitrin 3-β-d-glucose (1), limocitrin-3-α-l-rhamnose (2), 3,6-di-C-glucosylapigenin (3), narirutin (4), rutin (5) and narcissin (6) by UV, 1-NMR and 13C-NMR spectroscopy and sugar analysis. Each component was intravenously injected into SHR-SP rats (1 mg/100g body weight), and 3 and 5 were found to lower their blood pressure.Among these compounds, 2 and 3 were a new flavonol and flavone glycoside, respectively.

As a series of our studies on physiologically active substances in citrus fruit peels, we report here the differences between flavonoid glycosides in Citrus unshiu peelings (the ripe fruit peels) and flavonoid glycosides in young Citrus unshiu peelings (the unripe fruit peels). Eleven flavonoid glycosides were isolated from young Citrus unshiu peels and their structures established by UV, MS, 1H-NMR and 13C-NMR spectroscopy and also by chemical findings. They were limocitrin 3-β-D-glucoside (1). narirutin (4), rutin (5), narcissin (6), hesperidin (7), 3-hydroxy-5, 6, 7, 8, 3', 4'-hexamethoxyflavone 3-β-D-glucoside (8), 6, 8-di-C-glucosylapigenin (11), 3, 8-di-C-glucosylapigenin (12), 3, 7, 4'-trihydroxy-5, 6, 8, 3'-tetramethoxy flavone 3-β-D-glucoside (13), 3, 7, 4'-trihydroxy-5, 6, 8, 3'-tetramethoxyflavone 3-O- {[3-hydroxy-3-methylglutaryl (1→6)] -β-D-glucoside} (14) and limocitrin 3-O- {[3-hydroxy-3-methylglutaryl (1→6)] -β-D-glucoside} (15). Five flavonoid glycosides (11) (15) were found not to be present in Citrus unshiu peelings (the ripe fruit peels), but could be isolated from young Citrus unshiu peelings (the unripe fruit peels). Thus the kinds and quantity of flavonoid glycosides in ripe fruit peels and those in unripe fruit peels differ greatly. The relationship between their structures and hypotensive activity was determined by injecting the compounds intravenously in SHR-SP. Of these compounds, (13), (14), and (15) were identified here for the first time as flavonoid glycosides.

During the course of our studies on physiologically active substances in citrus fruit peels, seven phenyl propanoid glycosides were isolated from the lemon, unshiu and kinkan peels, and their structures were determined by MS, 1H-NMR and 13C-NMR spectroscopy, and chemical evidence. Their glycosides were coniferin [1], syringin [2], dehydrodiconiferyl alcohol-4-β-glucoside [3], citrusin A [4], citrusin B [5], citrusin C [6] and 3-(4-hydroxy-3-methoxyphenyl)-l-glucosyl-2-propene [7]. We propose the term citrusin D for the new phenyl propanoid glycoside [7]. Each component was intravenously injected to SHR-SP rats (1mg/100g body weight), and compounds [1] and [2] were found to raise blood pressure, but compounds [3], [4], [6] and [7] lowered blood pressure. Among these isolated compounds, [1]_??_[6] were found in the lemon, unshiu and kinkan peelings for the first time.

During the course of our studies on physiologically active substances in citrus fruit peels, five monoterpenoid glycosides were isolated from orange, hassaku and yuzu peels, and their structures were established by MS, 1H-NMR and 13C-NMR spectroscopy, and chemical evidences:namely trans-carveol 6-β-D-glucopyranoside[1], α-terpineol 8-β-D-glucopyranoside[2], (2E, 6R)-2, 6-dimethyl-2, 7-octadien-6-ol-1-O-β-D-glucopyranoside(9-hydroxylinalool 9-β-glucopyranoside) [3], vomifoliol 9-O-β-glucopyranoside [4] and (6R, 7E, 9R)-9-hydroxymegastigma-4, 7-dien-3-one-9-O-β-D-glucoside[5].Among these [1 ] and [2] are new monoterpenoid glycosides, whereas [3], [4] and [5] were isolated from orange, hassaku and yuzu peels, respectively for the first time.

As one of the studies on physiological acitive substances in citrus peel, the present paper describes structures and hypotensive effects of flavonoid glycosides on zabon, grapefruit and hassaku peels. Five flavonoid glycosides were isolated and their structures were established as 6, 8-di-C-glucosylapigenin (1), 3, 8-di-C-glucosylapigenin (2), limocitrin 3-O- {[5-α-glucosyl-3-hydroxy-3-methylglutaryl (1→2)] -β-glucoside} (3), apigenin 7- [2-O-α-rhamnosyl-β-glucoside] (4) and naringenin 7-β-glucoside (5) by UV, 1H-NMR and BC-NMR spectroscopies and chemical evidence. Compounds 4 and 5 were intravenously injected in SHR-SP (1.0mg dose/100g body weight), and 4 was found to lower rat blood pressure.

We describe the structures and hypotensive effects of three additional glycosides (1, 2 and 3) obtained through further investigation on unshiu peelings. The structures 3-hydroxy-3', 4', 5, 6, 7, 8-hexamethoxyflavone 3-β-D-glucoside (1), limocitrin 3-O- [5-α-glucosyl-3-hydroxy-3-methylglutaryl (1→2)] -β-glucoside (2) and narirutin-4'-glucoside (3) were established by UV, 1H-NMR and 13C-NMR spectroscopy, and chemical evidence. Compounds 1 and 3 showed strong depressive effects, when intravenously injected with stroke-prone spontaueously hypotensive rats (0.51.0mg dose/100g body weight). Among these compounds, 1 was a new flavonoid glycoside, and 2 anal 3 were found for the first time in unshiu.

(1981). Monoterpenoid and Sesquiterpenoid Constituents of the Essential Oil of Sugi (Cryptomeria Japonica D. DON.) Agricultural and Biological Chemistry: Vol. 45, No. 6, pp. 1493-1495.

The structure of flavonoids in hot water extracts of sudachi (Citrus sudachi) peels were investigated. The physiological activity of the extracts was tested on stroke-prone spontaneously hypotensive rat (SHR-SP). The separation and purification of flavonoids were conducted by solvent extraction, precipitation by lead subacetate, gel filtration on TSK gel HW-40 F and column chromatography on silica gel. Six constituents were isolated, and their structures were hesperidin (1), neohesperidin (2), hesperetin-7-O-{[α-rhamnosy l (1→2)]-[α-rhamnosyl (1→6)]-β-glucose} (3), sudachiin A (4), 3, 8-di-C-glucosylapigenin (5) and 3, 8-di-C-glucosyldiosmetin (6) by UV, MS, 1H-NMR and 13C-NMR spectroscopy and sugar analysis. Among these compounds, 3, 5 and 6 were new flavonoid glycosides. Each component was intravenously injected in SHR-SP (1 mg/100g of body weight). Constituent 4 lowered blood pressure.

When chlorella was treated with alkali after decolorization by methyl alcohol and then fractionated by gel filtration, the fraction showed a depressive effect. The blood pressure of SHRSP and SHR showed a fall of an average of 63 mmHG 1 hour after intravenous administration, 47 MMHg 2 hours after intraperitoneal administration. The blood pressure of normotensive Wistar rats also showed a fall of an average of 32 mmHg 1 hour after intravenous administration.

The hypotensive substance in a chlorella hot water extract was fractionated by ultrafiltration, Sepharose-2B, ultracentrifugation and density-gradient isoelectric focusing. On the basis of component analysis, the purified substance was considered to be a macromolecular glycoprotein.At high concentrations, this substance inhibited contractions, caused by ACh (8×10-3g/ml), NE (3×10-3g/ml) and Ca (2×10-3g/ml), but it did not inhibited contractions cuased by K. Its hypotensive action is due to its direct effect upon the blood vessels.

A macromolecular hypotensive substance in water extract of Fomes pinicola was purified by sequential fractionation on columns of Sephadex G-75, DEAE-cellulose, Sephadex G-150, Hydroxyapatite and Sepharose CL-4B gels. On the basis of its chemical properties and component analysis, it was considered to be a glycoprotein containing a large proportion of carbohydrate.

We tried to obtain hypotensive substances in hot water or cold water extracts from seventy items of fifty five plants. Administered intravenously, fractions from mandarine orange leaves, lily bulbs, bamboo grass, spirulina, leek, bean sprout, chlorella, fomitopsis pinicola, mandarine orange peels, young barley leaves, persimmon leaves, and tomato plant leaves showed marked falls in blood pressure.

We compared the hypotensive effects of fractions with molecular weights of 500 to 1, 000 obtained from hot water extracts from twelve kinds of citrus peel. Intravenous administration of fractions from mandarine orange, lemon, grapefruit, yuzu, orange, iyokan, narutokan and sudachi showed marked falls of blood pressure in SHR and SHRSP. Furthermore, we fractionated the fraction from lemon peel by HPLC, and isolated a compound which is considered to be a fravonoid.